As a sometimes ill-equipped but always devoted single parent to his two adolescent daughters, Grace and Natalie, Wade is taking the major step of dating again. His supportive and compassionate best friends, Forrest and his wife, Delia, and Ben and his wife, Michelle, are thrilled he’s resurfaced and enthusiastically offer to help set up his online profile.
Wade suddenly finds himself in a "relationship" he has no interest in when he has trouble turning down a second date. Also, Wade tries to understand when Grace struggles with her social media posts.
When Wade’s friends encourage him to join a support group for partners who have lost a spouse to help him deal with his anger, Wade’s shocked by the advice he’s given by the host of the support group, Caroline.
When Wade changes the password to his online dating profile because his friends become too involved, Forrest goes to great lengths to keep tabs on him. Also, Grace and Natalie are torn when their favorite romance-themed reality show they watched with their mom returns for a new season.
Grace gets the lead in the school musical, but Wade realizes that the teachers are giving her special treatment after he hears her sing. Also, Michelle and Ben persuade Delia and Forrest to volunteer for the chaotic snack bar duty at a school function.
When Wade visits a local hot spot to meet people instead of using his dating app, Forrest and Ben decide to be his wing men.
When Wade goes out of town for the day, he panics at the realization that he is the sole caretaker of his children. Also, Delia picks up the girls from school for Wade but is thrown for a loop when Grace tells a clever lie to hang out with her friends.
Wade and the girls tackle hosting a traditional Thanksgiving dinner for friends and extended family. Also, Ben attempts to make a fried turkey for the first time.
Wade pretends to be dating Caroline to avoid being set up on blind dates by Delia. Also, Ben and Michelle throw an anniversary party for themselves, but have issues with the catering.
Wade is giddy, his daughters are amused and his friends are excited when he has his first crush since becoming single again. Also, Grace and Natalie take advantage of their dad going on dates by having friends over and it starts to get out of hand.
Wade considers moving his relationship forward with Anna if his daughters approve of her after they all meet. Also, Delia, Grace and Natalie realize how priceless their memories are of Jill are as they prepare to sell some of her belongings at a garage sale.
The women from the Widow’s Support Group offer Wade unexpected advice for getting out of his dating rut. Also, while Michelle is recovering from gallbladder surgery, Delia relentlessly pushes her to follow strict medical advice.
When Wade decides to redo his will, he is conflicted about who should get custody of his children. Also, Michelle tries to convince Ben to get a vasectomy after they have a pregnancy scare.
Wade convinces Forrest to take his career advice, and the results are disastrous. Also, Ben lands a lucrative opportunity for his company, but Michelle is uncomfortable embracing their success.
When Wade has a bad date with Natalie's friend's mother, Natalie ends up paying the price. Also, Forrest finds unusual ways to fill his time during his unemployment, and Ben has a conflict with his daughter Sahai's basketball coach.
When Wade lands a job for Denny, a newly divorced, wealthy client, he realizes Denny is only interested in using Wade to meet women. Also, Meg applies her expertise as an accountant to get Wade's finances on track, and Forrest and Delia attempt to clear the tension between them by having an argument.
Wade analyzes his feelings about his casual relationship with Caroline. Also, Delia and Michelle help Grace work through an awkward middle-school phase.
As Grace prepares to attend her first dance, Wade strongly feels Jill's absence and leans on his friends to get through it. Also, Wade, Forrest, Delia, Ben and Michelle reflect on growing older and the changes their lives have undergone in the past year.
After Wade has an instant connection with a woman he met briefly in a parking lot, he’s determined to find her again. Also, Michelle waits to hear from the colleges she applied to for her business degree, and Natalie tries to convince Wade she’s old enough to get her ears pierce.
When Wade goes on a date with Shannon, he learns quickly that he has to come to terms with her unusual living arrangements if he wants to keep seeing her. Also, Grace is struggling with fitting in at her new high school, Michelle grapples with her algebra college course and Delia tries to help Forrest fit in with his much younger colleagues.
After Forrest gifts a water gun to Noah, Ben and Michele quickly take it away; the group has a frank discussion about racial injustice; Wade is trying to figure out how to celebrate Shannon's birthday since their relationship is so new.
After Ben recommends Wade for a job on the same work site he’s on, they are surprised by their wildly different professional styles. Also, Delia is struggling to not be so judgmental about how Michelle is raising her kids.
When Wade decides to introduce Shannon to his friends, the get together quickly takes an awkward turn. Also, Noah tries to fit in with the older kids since he’s tired of being one of the babies, and Forrest overindulges in edibles.
Wade wants to invite Shannon to spend the night, but first he needs to figure out how to discuss it with Natalie and Grace. Also, Ben becomes jealous of all the attention Michelle is giving to her school work and study group.
Delia and Forrest decide to play tennis to add some camaraderie to their relationship, but instead get wildly competitive. Also, when Wade tries to teach Grace to drive, she’s reluctant to learn and confesses the surprising reason why to Michelle.
While the friends are at an escape room for a fun evening, Wade has an embarrassing slip of the tongue that creates an uncomfortable situation for Shannon.
After Wade helps Shannon’s ex-husband find a job, his assistance has unintended consequences for their relationship.
Natalie realizes that her memories of her mom are starting to fade when Michelle and Delia have a memorial to honor Wade’s wife. Also, Forrest and Ben get competitive when their kids enter a fundraising contest at school.
When Wade and Shannon have trouble connecting while they are living far apart, he is forced to consider the realistic future of their relationship. Also, Forrest starts suffering from insomnia and doesn’t know how to tell Delia that she is the reason.
Wade, Forrest and Ben decide to schedule colonoscopy appointments at the same time after they learn that Ben is scared to go. Also, Michelle tries to avoid her sister Meg’s boyfriend drama, but Delia winds up getting over-involved in Meg’s issues.
Wade comes to terms with putting his relationship with Shannon in the past and starts dating again. Also, Delia realizes why she has been so controlling her whole life, and Michelle takes on the role of managing Ben’s business finances. Season Finale.
